Before you know it, we’ll be in the crisp days of fall. To kick off the new season, I’ve curated a series of posts featuring the shoes I’ll be pairing with my fall transitional outfits, along with a few styling ideas.

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Studded Ballet Flats Three Ways

My Sizing: I’m 4’10”, and my bust, waist, and hip measurements are 32″, 24″, and 36″. My inseam is 25″ (the measurement from the inside of my leg to my ankle bone). The clothes shown are unaltered and show how they fit me right from the store. I list my sizing beside each item to help you compare when shopping online. When referencing my true size, that is often the smallest option available at a brand or petite xxs/00/24. I wear a size 5 shoe.

Studded Ballet Flats

Ballet flats and mary jane flats continue to be popular for fall 2025. The sleek profile of a pair of flats makes them perfect for petites. They don’t add bulk to an outfit, so they pair well with dresses, skirts, and pants of nearly any length. You can pair them with your cropped pants and jeans or tuck them under a full-length drapey pair. A ballet flat can be a workhorse in your transitional wardrobe – perfect for mild weather and a versatile choice that can go with just about everything in your closet.

Greta Ballet Flats

In this post, I’m styling a pair of studded ballet flats from Madewell in three different outfits. Just like the leopard flats, I paired them with a dress, and in this case, I went with two different styles of jeans: barrel and cropped flare. The Greta Ballet Flats are soft and supportive, available in several colors, including options without studs. The studded pair adds a statement to an outfit, but they’re still fairly neutral.

J.Crew Factory Knit Mixy Dress

  • Size Wearing: XXS in Burnt Cinnamon
  • Fit: true to size
  • Fabric & Care: 57% cotton/38% TENCEL™ Modal/5% elastane bodice 100% cotton skirt | Machine Washable

I love wearing ballet flats with dresses. The dress I’m wearing here is from J.Crew Factory and in regular sizing, it’s a great length for petites. The top is stretchy and ribbed and fits well at the arm openings. The skirt is 100% cotton. I styled this outfit for a mild weather day with a cotton sweater from Quince worn over the shoulders.

Early fall outfit featuring a red dress styled with a white sweater draped over the shoulders and studded ballet flats, showcasing a chic transitional look and fall shoe trend

Flats TTS | Dress XXS | Sweater XS in ivory

J.Crew Charley Kickout Cropped Jeans

  • Size Wearing: 24 Petite in Storm Wash
  • Fit: true to size
  • Inseam: 25.5″ in petite
  • Rise: 10 ” in petite – I find the rise to be lower than the stated 11.5″ rise on the J.Crew website
  • Fabric & Care: 99% cotton/1% Lycra® spandex | Machine Washable

The Charley Kickout Cropped Jeans are a cropped flare that is cropped just below the ankle bone – instead of above. I love the longer length and overall shape of the jeans. They’re 99% cotton with 1% Lycra for light stretch. They are overall true to size. On my shape (24″ waist, 36″ hips), they are loose at my waist, but tight across my hips and thighs. They loosen with wear, but don’t bag out, so although they’re a bit snug on my hips and thighs, I still find my true size to be a comfortable fit. To note the classic length of these jeans have a 27.5″ inseam, so if you’re ok with the 11.5″ rise on that pair, they could be a perfect full-length flare to wear with flats in the regular length. This style of jeans looks great with ballet flats, but will also pair well with boots. I paired them here with a simple classic white button down from J.Crew Factory. This top has a tailored fit and is great for wearing alone or layered. It’s a little bit sheer, but not see-through if you wear a nude bra.

Casual fall outfit featuring light wash cropped flare jeans, a classic white button-down shirt, and studded ballet flats — a laid-back way to style studded flats for early fall.

Jeans Petite 24 in storm wash | Top Petite XXS | Flats TTS | Bag (Polene) similar linked here

Madewell Pieced Barrel-Leg Jeans

  • Size Wearing: 24 Petite in Tile White
  • Fit: true to size
  • Inseam: 25″ in petite
  • Rise: 10 ” in petite
  • Fabric & Care: 100% cotton | Machine Washable

If you’re interested in trying barrel jeans, I find the Pieced Barrel-Leg Jeans from Madewell to be the best balance for me personally. The length comes to my ankle bone, and the leg is tapered, but not dramatic. You can wear white year-round, but you could also swap in the same jeans in black for this outfit. I paired them with a short-sleeve cashmere sweater from Quince and a cropped denim top.

Petite-friendly casual early fall outfit featuring white barrel leg jeans, a cashmere short-sleeve sweater layered with a cropped denim top, and studded ballet flats — a relaxed way to wear studded flats this season.

Flats TTS | Denim Top XXS | Jeans Petite 24 | Cashmere T-Shirt XS in oatmeal | Bag (Polene) similar linked here

I’m still searching for a neutral ballet flat I love, but I plan to style them in a future post when I find a winning pair! I also plan to style sneakers as part of this series. Stay tuned!